JP6467288B2 - 硬化性組成物及びその硬化物 - Google Patents
硬化性組成物及びその硬化物 Download PDFInfo
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- JP6467288B2 JP6467288B2 JP2015103925A JP2015103925A JP6467288B2 JP 6467288 B2 JP6467288 B2 JP 6467288B2 JP 2015103925 A JP2015103925 A JP 2015103925A JP 2015103925 A JP2015103925 A JP 2015103925A JP 6467288 B2 JP6467288 B2 JP 6467288B2
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- 239000000203 mixture Substances 0.000 title claims description 119
- 229920000642 polymer Polymers 0.000 claims description 238
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 123
- 239000000178 monomer Substances 0.000 claims description 81
- 239000004014 plasticizer Substances 0.000 claims description 51
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 28
- 239000000463 material Substances 0.000 claims description 28
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 25
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 22
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 22
- 230000009477 glass transition Effects 0.000 claims description 14
- 229920001519 homopolymer Polymers 0.000 claims description 14
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 9
- 239000000377 silicon dioxide Substances 0.000 claims description 8
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 7
- 238000004078 waterproofing Methods 0.000 claims description 6
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- -1 acrylic ester Chemical class 0.000 description 146
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- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 22
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- 239000007795 chemical reaction product Substances 0.000 description 8
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
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- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 description 6
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 6
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- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 4
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- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- ARKBFSWVHXKMSD-UHFFFAOYSA-N trimethoxysilylmethanamine Chemical compound CO[Si](CN)(OC)OC ARKBFSWVHXKMSD-UHFFFAOYSA-N 0.000 description 1
- OJAJJFGMKAZGRZ-UHFFFAOYSA-N trimethyl(phenoxy)silane Chemical compound C[Si](C)(C)OC1=CC=CC=C1 OJAJJFGMKAZGRZ-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 description 1
- YZYKZHPNRDIPFA-UHFFFAOYSA-N tris(trimethylsilyl) borate Chemical compound C[Si](C)(C)OB(O[Si](C)(C)C)O[Si](C)(C)C YZYKZHPNRDIPFA-UHFFFAOYSA-N 0.000 description 1
- 235000021081 unsaturated fats Nutrition 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 239000012855 volatile organic compound Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- 150000003755 zirconium compounds Chemical class 0.000 description 1
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Description
(1) 一般式(1):−SiR1 aX3-a (1)
(式中、R1は、炭素数1〜20の置換または非置換の炭化水素基を表す。Xは、それぞれ独立に水酸基または加水分解性基を表す。aは、0または1を示す。)
で表される反応性ケイ素基を1分子中に平均して1個より多く有するオキシアルキレン系重合体(A)、及び、一般式(1)で表される反応性ケイ素基を有し、反応性ケイ素基当量が0.30mmol/g以上である(メタ)アクリル酸エステル系重合体(B)、および、酸化チタン(D)を含有し、重合体(A)及び(B)の合計100重量部に対して酸化チタン(D)を50重量部以上200重量部以下含有する硬化性組成物、
(2)重合体(A)が、反応性ケイ素基を1分子中に平均して1.4個以上有する(1)に記載の硬化性組成物、
(3)重合体(A)が、1つの末端部位に平均して1個より多い反応性ケイ素基を有する(1)または(2)に記載の硬化性組成物、
(4)重合体(B)を構成する単量体が、ホモポリマーのガラス転移温度が50℃以上であり反応性ケイ素基を有さない単量体(b1)を50重量%以上含有する(1)〜(3)のいずれか1つに記載の硬化性組成物、
(5)重合体(B)を構成する単量体が、ホモポリマーのガラス転移温度が80℃以下であり反応性ケイ素基を有さない単量体(b2)を30重量%以上含有する(1)〜(3)のいずれか1つに記載の硬化性組成物、
(6)重合体(B)の反応性ケイ素基当量が0.50mmol/g以上である(1)〜(5)のいずれか1つに記載の硬化性組成物、
(7)さらに、反応性ケイ素基を1分子中に平均して0〜1個有する高分子量可塑剤(C)を含有する(1)〜(6)のいずれか1つに記載の硬化性組成物、
(8)重合体(A)及び(B)の合計100重量部に対して、酸化チタンを100重量部以上含有する(1)〜(7)のいずれか1つに記載の硬化性組成物、
(9)
酸化チタン(D)が、シリカ、アルミナおよびジルコニアからなる群から選ばれる1種以上を用いて表面処理されたものである(1)〜(8)のいずれか1項に記載の硬化性組成物、
(10)(1)〜(9)のいずれか1つに記載の硬化性組成物を含む塗膜防水剤、
(11)(1)〜(9)のいずれか1つに記載の硬化性組成物から得られる硬化物、
に関する。
オキシアルキレン系重合体(A)は、以下の一般式(1):
−SiR1 aX3-a (1)
(式中、R1は、炭素数1〜20の置換または非置換の炭化水素基を表す。Xは、それぞれ独立に水酸基または加水分解性基(好ましくは加水分解性基)を表す。aは、0または1を示す。)
で表される反応性ケイ素基を有する。
原料となるポリオキシアルキレン(以下、「前駆重合体」ともいう)に不飽和結合を導入し、この不飽和結合にヒドロシラン化合物をヒドロシリル化反応により付加させる方法が挙げられる。不飽和結合の導入方法には特に限定は無く、例えば、水酸基等の官能基を有する前駆重合体に、この官能基と反応して結合を形成する基および不飽和結合を有する化合物を反応させ、不飽和結合を含有する重合体を得る方法;不飽和結合を有する単量体を重合させる方法;等が挙げられる。
水酸基、アミノ基、不飽和結合等の官能基を有する前駆重合体と、その官能基と反応して結合を形成する基(以下、「反応性基」ともいう)および反応性ケイ素基の両方を有する化合物(シランカップリング剤)とを反応させる方法が挙げられる。前駆重合体の官能基とシランカップリング剤の反応性基の組合せとしては、水酸基とイソシアネート基、水酸基とエポキシ基、アミノ基とイソシアネート基、アミノ基とチオイソシアネート基、アミノ基とエポキシ基、アミノ基とα,β−不飽和カルボニル基(マイケル付加による反応)、カルボキシ基とエポキシ基、不飽和結合とメルカプト基等が挙げられるがこれに限らない。
−NR2−C(=O)− (3)
(式中、R2は炭素数1〜10の有機基または水素原子を表す)で表されるアミドセグメントを含んでいてもよい。
Z−R3−SiR1 aX3-a (4)
(式中、R1、Xおよびaは、前記と同じである。R3は、2価の有機基、好ましくは炭素数1〜20の2価の炭化水素基である。Zは、水酸基、カルボキシ基、メルカプト基、1級アミノ基または2級アミノ基である。)で表されるケイ素化合物のZ基を、合成した重合体のイソシアネート基の全部または一部に反応させる方法を挙げることができる。
O=C=N−R3−SiR1 aX3-a (5)
(式中、R3、R1、Xおよびaは、前記と同じである。)で示される反応性ケイ素基含有イソシアネート化合物を反応させる方法を挙げることができる。
(a)末端に水酸基を有するポリオキシアルキレン(前駆重合体)と不飽和結合を有するエポキシ化合物とを反応させて、前駆重合体の末端に不飽和結合および水酸基を導入し、
(b)水酸基と反応して結合を形成する基(例えばハロゲン原子)および不飽和結合を有する化合物と得られた重合体とを反応させて、重合体の末端に複数の不飽和結合を導入し、
(c)複数の不飽和結合にヒドロシラン化合物をヒドロシリル化反応により付加させる
方法が挙げられる。
(メタ)アクリル酸エステル系重合体(B)は、一般式(1)で表わされる反応性ケイ素基を有し、反応性ケイ素基当量が0.30mmol/g以上である。なお本発明において「(メタ)アクリル」とは「アクリルおよび/またはメタクリル」を表わす。加水分解性基の説明は、重合体(A)における説明と同じである。
単量体(b1)のホモポリマーのガラス転移温度は、好ましくは50℃〜250℃、より好ましくは55℃〜200℃、さらに好ましくは60℃〜150℃である。
(I)重合性不飽和結合と反応性ケイ素基を有する化合物を、(メタ)アクリル酸エステルとともに共重合する方法。
(II)連鎖移動剤として、上述の反応性ケイ素基とメルカプト基を有する化合物の存在下、(メタ)アクリル酸エステルを共重合する方法。
(III)重合性不飽和結合と反応性官能基(Z基)を有する化合物(例えば、アクリル酸、アクリル酸2−ヒドロキシエチル)を、Z基を有さない(メタ)アクリル酸エステルとともに共重合した後、反応性ケイ素基とZ基に反応する官能基を有する化合物(例えば、イソシアネートシラン化合物)を反応させる方法。
(IV)リビングラジカル重合法によって(メタ)アクリル酸エステルを重合した後、分子鎖末端に反応性ケイ素基を導入する方法。
本発明の硬化性組成物は、反応性ケイ素基を1分子中に平均して0〜1.5個有する高分子量可塑剤(C)を含有してもよい。高分子量可塑剤(C)の添加により、硬化性組成物の粘度や硬化物の伸びを調整できる。
本発明の硬化性組成物は、補強剤として酸化チタン(D)を含有する。酸化チタンの添加により、硬化物の引張り物性や引裂き強度を向上できる。
本発明の効果を阻害しない限り、本発明の硬化性組成物は上述の重合体(A)、重合体(B)および酸化チタン以外の成分(その他の成分)を含有していてもよい。以下、その他の成分について説明する。
数平均分子量が約2,000のポリオキシプロピレンジオールを開始剤として使用し、亜鉛ヘキサシアノコバルテートグライム錯体触媒にてプロピレンオキシドの重合を行い、数平均分子量約28,500のポリオキシプロピレンジオールを得た。続いてこのポリオキシプロピレンジオールの水酸基1当量に対して1.0当量のNaOMeを含有するメタノール溶液を添加してメタノールを留去し、続いて1.0当量のアリルグリシジルエーテルを添加して130℃で2時間反応を行った。その後、0.28当量のナトリウムメトキシドを含有するメタノール溶液を添加し、メタノールを除去した後、さらに1.79当量の3−クロロ−1−プロペンを添加して末端の水酸基をアリル基に変換した。以上により、1つの末端部位に炭素−炭素不飽和結合を平均2.1個有するポリオキシプロピレンを得た。次に得られた重合体100重量部に対して白金ジビニルジシロキサン錯体(白金換算で3重量%のイソプロパノール溶液)36重量ppmを加え、撹拌しながら、ジメトキシメチルシラン1.9重量部をゆっくりと滴下し、90℃で2時間反応させた後、未反応のジメトキシメチルシランを減圧下留去することにより、末端がジメトキシメチルシリル基であり、1分子当たりの反応性ケイ素基数が3.2であり、数平均分子量が28,500である直鎖状のポリオキシプロピレン(重合体(A−1))を得た。
攪拌機を備えた四口フラスコにイソブタノール48.6重量部を入れ、窒素雰囲気下、105℃まで昇温した。そこに、メチルメタクリレート65.0重量部、2−エチルヘキシルアクリレート25.0重量部、3−メタクリロキシプロピルトリメトキシシラン10.0重量部、3−メルカプトプロピルトリメトキシシラン8.0重量部、および2,2’−アゾビス(2−メチルブチロニトリル)2.5重量部をイソブタノール22.7重量部に溶解した混合溶液を5時間かけて滴下した。さらに105℃で2時間重合を行い、1分子中に平均して1.8個のトリメトキシシシリル基(反応性ケイ素基)を有し、反応性ケイ素基当量が0.75mmol/gであり、数平均分子量が2,400であるポリ(メタ)アクリル酸エステル(重合体(B−1))のイソブタノール溶液(固形分60重量%)を得た。
攪拌機を備えた四口フラスコにイソブタノール24.4重量部を入れ、窒素雰囲気下、105℃まで昇温した。そこに、メチルメタクリレート20.0重量部、n−ブチルメタクリレート36.0重量部、ステアリルメタクリレート32.0重量部、3−メタクリロキシプロピルトリメトキシシラン12.0重量部、および2,2’−アゾビス(2−メチルブチロニトリル)4.5重量部をイソブタノール43.0重量部に溶解した混合溶液を5時間かけて滴下した。さらに105℃で2時間重合を行い、1分子中に平均して2.9個のトリメトキシシシリル基(反応性ケイ素基)を有し、反応性ケイ素基当量が0.48mmol/gであり、数平均分子量が6,300であるポリ(メタ)アクリル酸エステル(重合体(B−2))のイソブタノール溶液(固形分60重量%)を得た。
ブタノールを開始剤として使用し、亜鉛ヘキサシアノコバルテートグライム錯体触媒にてプロピレンオキシドの重合を行い、数平均分子量7,000のポリオキシプロピレンを得た。続いてこの水酸基末端ポリオキシプロピレンの水酸基1当量に対して1.2当量のNaOMeを含有するメタノール溶液を添加し、メタノールを留去した後、さらに1.5当量の3−クロロ−1−プロペンを添加して末端の水酸基をアリル基に変換した。次に得られたアリル基末端ポリオキシプロピレン100重量部に対して白金ジビニルジシロキサン錯体(白金換算で3重量%のイソプロパノール溶液)36重量ppmを加え撹拌しながら、ジメトキシメチルシラン1.72重量部をゆっくりと滴下した。その混合溶液を90℃で2時間反応させることにより、末端がジメトキシメチルシリル基であり、1分子あたりの反応性ケイ素基数が平均0.7であり、数平均分子量が7,000であり、分子量分布(Mw/Mn)が1.2である直鎖状のポリオキシプロピレン(高分子量可塑剤(C−1))を得た。
合成例1で得られた重合体(A−1)60.0重量部と合成例2で得られた重合体(B−1)のイソブタノール溶液66.7重量部を混合して、イソブタノールを減圧留去し、重合体(A−1)/重合体(B−1)の重量比が60/40である重合体混合物を得た。この重合体混合物100重量部に対して、合成例4で得られた高分子量可塑剤(C−1)30重量部、ポリ(メタ)アクリル酸エステル(東亜合成(株)製、商品名:UP−1080)20重量部、酸化チタン(石原産業(株)製、商品名:タイペークR−820)120重量部、紫外線吸収剤(住友化学(株)製、商品名:スミソーブ400)1重量部、ヒンダードアミン系光安定剤(HALS)((株)ADEKA製、商品名:アデカスタブLA−63P)1重量部を混合して、充分混練りした後、混合物を3本ペイントロールに3回通して、各成分を分散させた。この後、120℃で2時間減圧脱水を行い、脱水した混合物を50℃以下に冷却後、冷却した混合物に脱水剤としてビニルトリメトキシシラン(Momentive(株)製、商品名:A−171)3重量部、接着性付与剤としてN−(2−アミノエチル)−3−アミノプロピルトリメトキシシラン(信越化学工業(株)製、商品名:KBM−603)5重量部、触媒としてジオクチル錫ジラウレート(日東化成(株)製、商品名:ネオスタンU−810)1重量部を加えて、実質的に水分の存在しない状態で混練した後、得られた組成物を防湿性のカートリッジ型容器に充填後に密封して、1成分型硬化性組成物を得た。
23℃、相対湿度50%で、硬化性組成物の粘度をBH型粘度計、ローターNo.7(東機産業社製)を用い、ローター回転数が2rpmまたは20rpmの時の粘度を測定した。その結果を表1に示す。
硬化性組成物を厚み3mmのポリエチレン製の型枠に気泡が入らないよう充填し、23℃、相対湿度50%で3日間、さらに50℃で4日間養生することにより硬化物を得た。得られた硬化物から、JIS K 6251に準拠して3号ダンベルを打ち抜き、引張り試験(引張り速度200mm/分、23℃、相対湿度50%)を行い、50%伸張時のモジュラス(M50)、破断時強度(TB)、破断時伸び率(EB)を測定した。その結果を表1に示す。
硬化性組成物を厚み3mmのポリエチレン製の型枠に気泡が入らないよう充填し、23℃、相対湿度50%で3日間、さらに50℃で4日間養生することにより硬化物を得た。得られた硬化物からJIS K 6252に準拠して、切込みなしアングル形試験片及びトラウザ形試験片をそれぞれ打ち抜き、切込みなしアングル形試験片は引張り速度500mm/分にて、トラウザ形試験片は引張り速度100mm/分にて引裂き強さを測定した。その結果を表1に示す。
表1に示す量で重合体(A−1)、重合体(B)、高分子量可塑剤(C)、酸化チタン(D)、炭酸カルシウム、紫外線吸収剤、ヒンダードアミン系光安定剤(HALS)、脱水剤、接着性付与剤、触媒を混合して硬化性組成物を調製し、実施例1と同様にして評価を行った。その結果を下記表に示す。
Claims (11)
- 一般式(1):−SiR1 aX3-a (1)
(式中、R1は、炭素数1〜20の置換または非置換の炭化水素基を表す。Xは、それぞれ独立に水酸基または加水分解性基を表す。aは、0または1を示す。)
で表される反応性ケイ素基を1分子中に平均して1個より多く有するオキシアルキレン系重合体(A)、及び、一般式(1)で表される反応性ケイ素基を有し、反応性ケイ素基当量が0.30mmol/g以上である(メタ)アクリル酸エステル系重合体(B)、および、酸化チタン(D)を含有し、重合体(A)及び(B)の合計100重量部に対して酸化チタン(D)を50重量部以上200重量部以下含有する硬化性組成物。 - 重合体(A)が、反応性ケイ素基を1分子中に平均して1.4個以上有する請求項1に記載の硬化性組成物。
- 重合体(A)が、1つの末端部位に平均して1個より多い反応性ケイ素基を有する請求項1または2に記載の硬化性組成物。
- 重合体(B)を構成する単量体が、ホモポリマーのガラス転移温度が50℃以上であり反応性ケイ素基を有さない単量体(b1)を40重量%以上含有する請求項1〜3のいずれか1項に記載の硬化性組成物。
- 重合体(B)を構成する単量体が、ホモポリマーのガラス転移温度が80℃以下であり反応性ケイ素基を有さない単量体(b2)を30重量%以上含有する請求項1〜3のいずれか1項に記載の硬化性組成物。
- 重合体(B)の反応性ケイ素基当量が0.50mmol/g以上である請求項1〜5のいずれか1項に記載の硬化性組成物。
- さらに、反応性ケイ素基を1分子中に平均して0個より多く、且つ0.7個以下有するオキシアルキレン系重合体である高分子量可塑剤、又は、反応性ケイ素基を有さない高分子量可塑剤(C)を含有する請求項1〜6のいずれか1項に記載の硬化性組成物。
- 重合体(A)及び(B)の合計100重量部に対して、酸化チタンを100重量部以上含有する請求項1〜7のいずれか1項に記載の硬化性組成物。
- 酸化チタン(D)が、シリカ、アルミナおよびジルコニアからなる群から選ばれる1種以上を用いて表面処理されたものである請求項1〜8のいずれか1項に記載の硬化性組成物。
- 請求項1〜9のいずれか1項に記載の硬化性組成物を含む塗膜防水剤。
- 請求項1〜9のいずれか1項に記載の硬化性組成物から得られる硬化物。
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